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When I want to know what clothes to wear in a given country at a specific time period, I usually check out the high and low temperatures for the month and then check out comparable temperatures at home.

The first time I went to Spain in January, I found out the typical temps in Madrid in January were similar to the temps in March and April in my town. I chose a wardrobe that I would wear during those months at home.

For the later, it depends on how well you handle heat and cold. I've been in shirt sleeves when I've seen Roman women wearing wool coats. As Peg says, check the temps and pack according to your internal thermostat.

Well it's difficult to look nice in button down shirts unless they're freshly ironed so tee shirts (or polo shirts) are the obvious choice. I see nothing wrong with anyone wearing tee shirts and I've noticed that most tourists do wear tee shirts as they are less likely to wrinkle.

That look is uber casual - unless you're a student. for an adult a polo shirt with collar and khakis are a much better choice for touring in large cities. Naturally everyone can wear whatever they want - but people that are more presentable do tend to get better service in restaurants and stores - esp nicer ones.

I'll stick to my tee shirts as I can wear them to work. I'm sure I'd get odd looks if I wore polo shirts to work (other than dress down Fridays) as they are way too casual for the office. I don't buy clothes that I wear only for travel; I pack what I already own.

Tees are very versatile - you can easily dress them up. A polo shirt will only ever be a polo shirt - it would look stupid to add pearls or other necklaces to a polo shirt. Whereas you can take a simple black tee, wear it for sightseeing in the day time and add jewelry or a scarf/pashmina for evening and have a respectable look.

Rasta - you and nytraveler can wear polo shirts and khakis. I do not wear khakis as they can become dirty quickly. I prefer black trousers for travel.

MPHS - I just returned from my second trip to Barcelona and have a couple of observations outside the "normal" travel packing advice.
1 - Even though I was envisioning sunny Spain and thinking of it as a warm weather destination, I had to remind myself when packing that it is still March and the locals think it is COLD! So if you show up in a sundress or sandals, you will definitely look out of place, even if you are comfortable temperature-wise.
2 - It seemed like the hotel, restaurants and shops were about 10 -20 degrees warmer than these places typically are at home. I freeze in a US hotel but the hotel here was stifling. So if you were not already planning to wear layers, reconsider!
3 - Remember you will likely be going out for dinner very late (10 or 11), long after the sun has set - so you will need something warm if you are walking to dinner.

Just take what you feel confortable with. I'm Spanish, and in general we are not so concerned with people's clothes (except in very posh areas). It's attitude that matters. For us, an "ugly American" is not one dressed casual, but the kind of tourist that considers himself superior to the rest of the people just because he's a tourist. For example, If there's a parade and people are waiting patiently for it to start, and a tourist wants to step in front of all of them 'because you all can watch this next year, while I'm a tourist'. (I witnessed that last year).
On the other hand, we tend to dress rather casually except in some environments as offices or church. I'm a teacher in a highschool, and I usually wear jeans and tees for work. Often I also wear trainers. Not a problem at all,either with kids, parents or administration.